Guesthouse vacation rentals in Fairfield County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Fairfield County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Guesthouse in Wilton

4.96 out of 5 average rating, 100 reviews

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 minutes to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is a quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and dishwasher drawer. The bedroom has a queen bed and the living room has a futon couch which folds down. We also have a twin air mattress. It is perfect for one or two people.

Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 273 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Guest favorite

Guesthouse in Bedford Hills

4.91 out of 5 average rating, 117 reviews

Barrett's Sanctuary

Airy, bright guest house with with access to a gunite pool*, patio and expansive backyard for practicing your short game, playing disc golf or other sports. Loft (accessible by spiral staircase) furnished with queen bed. Single bed in alcove off living room. Central air/heat. Washer/dryer. Kitchenette w/ dishwasher. Satellite TV. LR w/ stone fireplace. Minutes to train (1h to Manhattan) and highways. Shopping/restaurants nearby. Delivery available from Seamless, Instacart and more. *Nominal fee

Guest favorite

Guesthouse in Brewster

4.93 out of 5 average rating, 106 reviews

Sherwood Barn - close to ski mountain

Our guests stay on the SECOND floor of the barn in a 1200 Sq Ft, fully reno'd apt that sleeps 6. Located about 1 hour from NYC you will find peace and serenity in the middle of nature on this 4 acre estate (that also contains our main home) where you can get away from it all. unwind this way or visit local attractions like Thunder Ridge Ski Mountain, snowshoe/ X Country skiing, hike/bike/running trails, restaurants and local cafe's. Great oasis to kick back and spend time with family.

Guest favorite

Guesthouse in Norwalk

5 out of 5 average rating, 119 reviews

Private one bedroom cottage on Conn. seashore

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian friendly town; you don't even need a car while here.

Guest favorite

Guesthouse in Southbury

4.96 out of 5 average rating, 55 reviews

The Nest. Large studio in the Woods.

New large studio on secluded property at the end of the country road. Surrounded by trees and across the river from the National Audubon, bird sanctuary. 5 minutes from I-84. 4 minutes from town and 1 hour from Manhattan. Private, peaceful and restful. If you want to retreat to nature and rejuvenate your spirit this is the place for you. We look forward to hosting you in this lovely setting and sharing our favorite list of walking trails.

Guest favorite

Guesthouse in South Salem

5 out of 5 average rating, 67 reviews

Newly renovated guesthouse with a patio

Take it easy at this unique and tranquil getaway. Our property is located a 5-min walk from Truesdale lake with access to the beach, hikes in the nearby parks, and many shops and restaurants to explore in Ridgefield, CT. Come and enjoy the serenity of the area while relaxing in this bright and spacious cottage. The guesthouse has 1 king-size bed and a queen size pull out couch.

Guest favorite

Guesthouse in Brewster

5 out of 5 average rating, 291 reviews

The Cottage by the Lake: Hudson Valley Indulgence

The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.

Guest favorite

Guesthouse in Bedford

4.93 out of 5 average rating, 179 reviews

Private Guest Studio

Just 39 miles north of Manhattan. Relax and unwind, to enjoy endless opportunity for outdoor activities, fine dining, antiquing, or just loving the peace & quiet of this private studio, in a manicured setting, with wood burning stove, porch, heated pool (June-August), and private footpaths leading to an open field.

Superhost

Guesthouse in Washington

4.73 out of 5 average rating, 245 reviews

Tiny House Magic

Full kitchen w/stove, microwave, sink, mid sized fridge 2 skylights 32" flat screen "SMART" TV Wifi French doors Steam shower jacuzzi w/rainfall showerhead & radio Glassware/flatware/cooking utensils Island counter Queen bed **No reasonable offer refused. Message me for special deals on last minute travels**

Guest favorite

Guesthouse in South Salem

4.93 out of 5 average rating, 227 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

A unique private and quiet 2 bedroom (1 double bed, two single full beds) totally self contained apt,with sitting room, bathroom ,mud room and full eat in kitchen, in Shaker Hollow, a classic 1795 colonial.Stone patio overlooking 3 1/2 acres of garden and a meadow along with a large fire pit.

Guest favorite

Guesthouse in Fairfield

4.96 out of 5 average rating, 180 reviews

Southport, CT across from BEACH

Located at Southport beach on Westport Line, this renovated 1 bedroom apartment totally private located above the garage and includes a full kitchen with new appliance and d/w and central air. Bdrm with queen, fine cotton sheets and towels, marble bath open living room w views.